Mass Spectrometry-Based Characterization of New Spirolides from Alexandrium ostenfeldii (Dinophyceae)
Spirolides belong to a group of marine phycotoxins produced by the marine planktonic dinophyte Alexandrium ostenfeldii. Composed of an imine moiety and a spiroketal ring system within a macrocylcle, spirolides are highly diverse with toxin types that vary among different strains. This study aims to...
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MDPI AG
2020
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Online Access: | https://epic.awi.de/id/eprint/53078/ https://epic.awi.de/id/eprint/53078/1/Nieva_2020.pdf https://hdl.handle.net/10013/epic.02109a8a-43ce-4711-97d7-b3f4ced940f2 |
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ftawi:oai:epic.awi.de:53078 2024-09-15T18:10:01+00:00 Mass Spectrometry-Based Characterization of New Spirolides from Alexandrium ostenfeldii (Dinophyceae) Nieva, Joyce A. Tebben, Jan Tillmann, Urban Wohlrab, Sylke Krock, Bernd 2020-10-02 application/pdf https://epic.awi.de/id/eprint/53078/ https://epic.awi.de/id/eprint/53078/1/Nieva_2020.pdf https://hdl.handle.net/10013/epic.02109a8a-43ce-4711-97d7-b3f4ced940f2 unknown MDPI AG https://epic.awi.de/id/eprint/53078/1/Nieva_2020.pdf Nieva, J. A. , Tebben, J. orcid:0000-0002-2780-2236 , Tillmann, U. orcid:0000-0002-8207-4382 , Wohlrab, S. orcid:0000-0003-3190-0880 and Krock, B. orcid:0000-0003-4022-9101 (2020) Mass Spectrometry-Based Characterization of New Spirolides from Alexandrium ostenfeldii (Dinophyceae) , Marine Drugs, 18 , p. 505 . doi:10.3390/md18100505 <https://doi.org/10.3390/md18100505> , hdl:10013/epic.02109a8a-43ce-4711-97d7-b3f4ced940f2 EPIC3Marine Drugs, MDPI AG, 18, pp. 505, ISSN: 1660-3397 Article isiRev 2020 ftawi https://doi.org/10.3390/md18100505 2024-06-24T04:26:11Z Spirolides belong to a group of marine phycotoxins produced by the marine planktonic dinophyte Alexandrium ostenfeldii. Composed of an imine moiety and a spiroketal ring system within a macrocylcle, spirolides are highly diverse with toxin types that vary among different strains. This study aims to characterize the spirolides from clonal A. ostenfeldii strains collected from the Netherlands, Greenland and Norway by mass spectral techniques. The structural characterization of unknown spirolides as inferred from high-resolution mass spectrometry (HR-MS) and collision induced dissociation (CID) spectra revealed the presence of nine novel spirolides that have the pseudo-molecular ions m/z 670 (1), m/z 666 (2), m/z 696 (3), m/z 678 (4), m/z 694 (5), m/z 708 (6), m/z 720 (7), m/z 722 (8) and m/z 738 (9). Of the nine new spirolides proposed in this study, compound 1 was suggested to have a truncated side chain in lieu of the commonly observed butenolide ring in spirolides. Moreover, there is indication that compound 5 might belong to new spirolide subclasses with a trispiroketal ring configuration having a 6:5:6 trispiroketal ring system. On the other hand, the other compounds were proposed as C- and G-type SPX, respectively. Compound 7 is proposed as the first G-type SPX with a 10-hydroxylation as usually observed in C-type SPX. This mass spectrometry-based study thus demonstrates that structural variability of spirolides is larger than previously known and does not only include the presence or absence of certain functional groups but also involves the triketal ring system. Article in Journal/Newspaper Greenland Alfred Wegener Institute for Polar- and Marine Research (AWI): ePIC (electronic Publication Information Center) Marine Drugs 18 10 505 |
institution |
Open Polar |
collection |
Alfred Wegener Institute for Polar- and Marine Research (AWI): ePIC (electronic Publication Information Center) |
op_collection_id |
ftawi |
language |
unknown |
description |
Spirolides belong to a group of marine phycotoxins produced by the marine planktonic dinophyte Alexandrium ostenfeldii. Composed of an imine moiety and a spiroketal ring system within a macrocylcle, spirolides are highly diverse with toxin types that vary among different strains. This study aims to characterize the spirolides from clonal A. ostenfeldii strains collected from the Netherlands, Greenland and Norway by mass spectral techniques. The structural characterization of unknown spirolides as inferred from high-resolution mass spectrometry (HR-MS) and collision induced dissociation (CID) spectra revealed the presence of nine novel spirolides that have the pseudo-molecular ions m/z 670 (1), m/z 666 (2), m/z 696 (3), m/z 678 (4), m/z 694 (5), m/z 708 (6), m/z 720 (7), m/z 722 (8) and m/z 738 (9). Of the nine new spirolides proposed in this study, compound 1 was suggested to have a truncated side chain in lieu of the commonly observed butenolide ring in spirolides. Moreover, there is indication that compound 5 might belong to new spirolide subclasses with a trispiroketal ring configuration having a 6:5:6 trispiroketal ring system. On the other hand, the other compounds were proposed as C- and G-type SPX, respectively. Compound 7 is proposed as the first G-type SPX with a 10-hydroxylation as usually observed in C-type SPX. This mass spectrometry-based study thus demonstrates that structural variability of spirolides is larger than previously known and does not only include the presence or absence of certain functional groups but also involves the triketal ring system. |
format |
Article in Journal/Newspaper |
author |
Nieva, Joyce A. Tebben, Jan Tillmann, Urban Wohlrab, Sylke Krock, Bernd |
spellingShingle |
Nieva, Joyce A. Tebben, Jan Tillmann, Urban Wohlrab, Sylke Krock, Bernd Mass Spectrometry-Based Characterization of New Spirolides from Alexandrium ostenfeldii (Dinophyceae) |
author_facet |
Nieva, Joyce A. Tebben, Jan Tillmann, Urban Wohlrab, Sylke Krock, Bernd |
author_sort |
Nieva, Joyce A. |
title |
Mass Spectrometry-Based Characterization of New Spirolides from Alexandrium ostenfeldii (Dinophyceae) |
title_short |
Mass Spectrometry-Based Characterization of New Spirolides from Alexandrium ostenfeldii (Dinophyceae) |
title_full |
Mass Spectrometry-Based Characterization of New Spirolides from Alexandrium ostenfeldii (Dinophyceae) |
title_fullStr |
Mass Spectrometry-Based Characterization of New Spirolides from Alexandrium ostenfeldii (Dinophyceae) |
title_full_unstemmed |
Mass Spectrometry-Based Characterization of New Spirolides from Alexandrium ostenfeldii (Dinophyceae) |
title_sort |
mass spectrometry-based characterization of new spirolides from alexandrium ostenfeldii (dinophyceae) |
publisher |
MDPI AG |
publishDate |
2020 |
url |
https://epic.awi.de/id/eprint/53078/ https://epic.awi.de/id/eprint/53078/1/Nieva_2020.pdf https://hdl.handle.net/10013/epic.02109a8a-43ce-4711-97d7-b3f4ced940f2 |
genre |
Greenland |
genre_facet |
Greenland |
op_source |
EPIC3Marine Drugs, MDPI AG, 18, pp. 505, ISSN: 1660-3397 |
op_relation |
https://epic.awi.de/id/eprint/53078/1/Nieva_2020.pdf Nieva, J. A. , Tebben, J. orcid:0000-0002-2780-2236 , Tillmann, U. orcid:0000-0002-8207-4382 , Wohlrab, S. orcid:0000-0003-3190-0880 and Krock, B. orcid:0000-0003-4022-9101 (2020) Mass Spectrometry-Based Characterization of New Spirolides from Alexandrium ostenfeldii (Dinophyceae) , Marine Drugs, 18 , p. 505 . doi:10.3390/md18100505 <https://doi.org/10.3390/md18100505> , hdl:10013/epic.02109a8a-43ce-4711-97d7-b3f4ced940f2 |
op_doi |
https://doi.org/10.3390/md18100505 |
container_title |
Marine Drugs |
container_volume |
18 |
container_issue |
10 |
container_start_page |
505 |
_version_ |
1810447615156813824 |